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The Jake Long of 3 years ago is worth every bit of that. The injury ridled, declining Long of today isn't, sad because he's only 28 years old but the injuries have taken a toll on him. Not sure he'll ever regain form

I'll be in the minority, but I wouldn't have a problem with it if it were structured correctly. It'd have to include a huge roster bonus in place of a signing bonus for me. That is, if Long is still on the roster at the end of next season and he hasn't been injured or anything, he'd get the roster bonus. I'd probably structure it something like:

5 Years
Signing Bonus: 5 Million (Prorated 1 million/ year, dead cap of 4 million if cut after first year)
1st Year Salary: 3.5 Million (1st year guaranteed, which would escalate to an average of 7.8 million for the next 4 years)
1st Year Roster Bonus: 10 Million (One time, paid out after first year if not cut)

Total worth of that is around 50 million. If he shows that he comes back from injury after the first year, you would guarantee the next 2-3 years of salary. You could even list the option bonus as guaranteed in the contract so it would look better for Long, which would count against the second year cap if accepted but retroactively count against the first year cap if cut. If he doesn't come back from injury well you cut him/ trade him and have 4 million in dead cap space (plus the roster bonus if you list it as "likely to be earned"). He'd come out with about 20 million "guaranteed" with possibility for more.

I don't think Long would take it, because I think some team will give him what he wants regardless, but it's something. Also I used a roster bonus instead of an option bonus because I think a roster bonus would be more palatable to Long. No way he would agree to a 1st year option without a disincentive to the team (dead money).